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School agents—such as counselors and teachers—play a central role in supporting undocumented students’ college transitions. Supportive school agents, however, are not solely a product of an individual’s desire to engage in supportive practices. Rather, school agents are embedded within multilayered contexts which shape their ability to support undocumented students. This paper examines how the local context shapes school agent’s ability to support undocumented students’ college transitions through a case study of the Chicago metropolitan area. Finding the local contexts impacts school agents’ 1) knowledge level and access to resources, 2) challenges encountered in supporting undocumented students, and 3) ability to build trust with students, I argue, the local context is crucial to understanding the role of school agents.